Let Us Take You Away from Chicago with These Vacation Packages
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5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$335* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$392* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$404* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$407* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$407* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$453* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$454* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
7Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$506* Price subject to changes
per person based on 2-person occupancy
Updated:20 hours ago
Updated:20 hours ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$627* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$742* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$818* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$1,026* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$1,070* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$1,121* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
6Night(s) Trip
From Chicago Packages to Fort Myers
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Flight+Hotel
From
$426* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
6Night(s) Trip
From Chicago Packages to Fort Myers
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Flight+Hotel
From
$472* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$495* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
6Night(s) Trip
From Chicago Packages to Fort Myers
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Flight+Hotel
From
$513* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$577* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
6Night(s) Trip
From Chicago Packages to Fort Myers
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Flight+Hotel
From
$647* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
5Night(s) Trip
From Chicago Packages to Orlando
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Flight+Hotel
From
$723* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
6Night(s) Trip
From Chicago Packages to Fort Myers
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Flight+Hotel
From
$736* Price subject to changes
per person based on 2-person occupancy
Updated:day ago
Updated:day ago
7Night(s) Trip
From Chicago Packages to Cancun
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Flight+Hotel
From
$957* Price subject to changes
per person based on 2-person occupancy
Updated:8 hours ago
Updated:8 hours ago
7Night(s) Trip
From Chicago Packages to Houston
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Flight+Hotel
From
$544* Price subject to changes
per person based on 2-person occupancy
Updated:8 hours ago
Updated:8 hours ago
7Night(s) Trip
From Chicago Packages to Houston
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Flight+Hotel
From
$613* Price subject to changes
per person based on 2-person occupancy
Updated:8 hours ago
Updated:8 hours ago
7Night(s) Trip
From Chicago Packages to Houston
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Flight+Hotel
From
$676* Price subject to changes
per person based on 2-person occupancy
Updated:8 hours ago
Updated:8 hours ago
5Night(s) Trip
From Chicago Packages to Punta Cana
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Flight+Hotel
From
$983* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
7Night(s) Trip
From Chicago Packages to Houston
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Flight+Hotel
From
$993* Price subject to changes
per person based on 2-person occupancy
Updated:8 hours ago
Updated:8 hours ago
5Night(s) Trip
From Chicago Packages to Punta Cana
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Flight+Hotel
From
$1,012* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
5Night(s) Trip
From Chicago Packages to Punta Cana
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Flight+Hotel
From
$1,152* Price subject to changes
per person based on 2-person occupancy
Updated:14 hours ago
Updated:14 hours ago
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
